Process for increasing sugar yield in sugar cane

ABSTRACT

There is provided a novel method for increasing sucrose yield in sugar cane by treating sugar cane a few weeks prior to harvest with a polyalkylene glycol ester of Alpha -hydroxy, Beta , Beta , Beta -trichloroethanephosphonic acid.

United States Patent [1 1 [111 3,874,872

Kupelian Apr. 1, 1975 PROCESS FOR INCREASING SUGAR YIELD [56] ReferencesCited IN SUGAR CANE UNITED STATES PATENTS [75] Inventor: Robert HowardKupelian, Yardley. 3,556,762 1/1971 Humm 71/86 Pa, 3.619.166 11/1971Qucbcdeaux. Jr. 71/86 [73] Assignee: Amerlcan Cyanamid Company PrinmrExaminer-James 0. Thomas. Jr.

Stumlord, Conn.

Attorney. Agent, or FirmHarry H. Kline [22] Filed: Mar. 2, 1973 21 Appl.No.: 337,327 [57] ABSTRACT There is provided a novel method forincreasing sucrose yield in sugar cane by treating sugar cane a few [5}LS.CCI. 71/86 weeks prior to harvest with a polyulkylene glycol ester{2 gz' of oz-hydroxy, B,B,B-trichloroethanephosphonic acid.

5 Claims, N0 Drawings PROCESS FOR INCREASING SUGAR YIELD IN SUGAR CANEThe present invention relates to a novel method for increasing thesucrose yield of sugar cane by applying 5 H thereto an effective amountof a poly-alkylene glycol ester or mixture of esters of u-hydroxy whereIi is an integer from O to 3: and B,B,B-trichloroethanephosphonic acidhaving the for- 3. His-polypropylene glycol bis-a-hydrosy-3.3.3- mula:trichloroethane-diphosphonate having the structure:

sport neon H OH col from each of which the two hydroxyl groups have beenremoved. It is an integer from O to 3 and m is an integer of l to 3. orhigher. CHOH OH It is known that sugar yields can be increased by Lmodifying the physiological process of sugar cane. C1 C1 However. noneof the presently employed quaternary where I is 3 fi 3 G 3 and amines orammomum halides as CXClTlPlillCd in US. v 4 a 2 l Pat. Nos. 3.493.361and 3.660.072 is entirely satisfacand i from 0 to i mixtures thereof.

The active phosphonate or phosphonate mixture is preferably applied tocane stalks as a liquid spray. i.e..

wherein R R and R are residues of polyalkylene glyg 20 R OC H OC H O) 011 0 i-R tory as enhancing increased yields. If a class of compoundscould be provided which would enhance yield activity ofsugar cane. suchwould fulfill a long felt need in the ML an aqueous solution orsuspension prepared from a According to the process olthe invention, ithas been wcmlhlc fl f 0r cmfllsmflblc conccmmtc m found that certainpolyulkylunc glycul esters of amount sufficient to provide from about1.0 pound per phahydroxy beta. beta. beta-triehloroethanephosphosacre toP of the "wuvc phonic acid are unexpectedly highly effective for in-Hllwclfcrjslncc h phosphmwtcs chlphlycdilhlhc P creasing sucrose yieldin field grown sugar cane. particcuss 0t thls mvcnltmh are generallyhquldsh ulufly when they are dpplicd m thc youngcr growing may also beapplied to cane stalks either as neat or disparts of the ripening canestalks about tw t ten weeks solved in a small amount of solventutilizing the ultra bet-Om hdrvcst low volume or low volume technique ofapplication. In The phosphonates employed in the practice of the 40hhphchhmlsthe phhsphlhhtc ls p instant invention are known. These aredefined with P the lcchhlchl hlhtcrhll in thc form of discl'cctparticularly in the patent to Friedman. US. Pat. No. droplets havingmuss mcdhm dhlmctcr hclwcc" 25 3 3 06 issued on Apt 2 19 4 which isincomoand 150 microns. Low volume application is similar to rated byreference herein. Illustrative of the useful low Volume hpphcmhlhcxccptlhg that the active cumpounds phosphonic i 2 2 2 phosphonate isdissolved in a minor amount. generally hydroxyethyl)-bis-[ 2-(2-hydroxypropoxy)-lfrom about 5% to about by volume. of a relativelymethylethyl] ester; phosphonic acid, (2,2,2-trichlo nonvolatile solvent.such as xylene. Panasol AN-2. Esso l-hydrnxyethyl )-bi5-[2-(Z-hydruxycthyoxy) ethyl] c3- HAN, 01' Light Cycle Oil. and i8 applied USsuch in thC ter; phosphonic acid. (2.2.2-trichloro-l-hydroxyethyl formof discreet droplets having a mass median diame-2-(2-hydroxypropoxy)-l-methylethyl ester. diester 5O ter of 25 to I50 Imicrons. Advantageously. the phoswith 1.1 '-oxydi-2-propanol; phosphonicacid. (2.2.2- phonates employed in the process of the presentinventriehloro-l -hydroxyethyl)-. 2-(2-hydroxyethoxy) ethyl tion canalso be applied as aerosols or fogs using eonester. diester withdiethylene glycol; and a compound ventional formulations and equipment.selected from the group consisting of: In general. wettablc powders areprepared bydisl. tris-polycthylene glycol bis-a-hydroxy-Bfifisolving thephosphonate in a volatile solvent, such as trichloroethane diphosphonatehaving the structure: acetone or methylene chloride, and spraying thethus il l where R is OC H (OC. ,H O),,, C. ,H OH and n formed solutionon a finely divided carrier such as attaand :2 each represent an integerfrom 0. l. 2 or 3: clay. kaolin. talc, or diatomaceous earth andadmixing 2. bis-polypropropylene glycol a-hydroxy-Bfifitherewith fromabout 1'71 to 10% by weight of a surfactrichloroethanephosphonate havingthe structure: tant. A small amount of a dispersing agent. such assodium lignosult'omttc. may also be added. Surfactants which may be usedinclude: polyoxyethylene sorbitan fatty acid esters. polyoxycthylenesorbitol esters and alkyl phenoxy polyoxyethylene ethanol. lt is a goodpractice to disperse the aforementioned wettable powder in water andthen apply the same to sugar cane stalks in an amount sufficient toprovide from about 0.5 pound to about 8.0 pounds per acre of thephosphonate.

An alternative manner in which to utilize the active compounds of thepresent invention is as an emulsifiablc concentrate. This is about 25%to 40% by weight of the phosphonate in about 5071 to 65% by weight of asolvent. such as xylene and admixing therewith about 571 to l()/( byweight of an emulsifier, such as a polyoxyethylated nonylphenol or apolyoxyethylene derivative ot an aliphatic or aromatic hydroxy compound.The thus prepared concentrate is then generally dispersed in water forapplication as a liquid spray.

The present invention will be further illustrated. but not limited. bythe following example. Unless otherwise stated. the parts are by weight.I

EXAMPLE 1 The following procedure is used to determine the efficacy oftest compounds for increasing sucrose yield in sugar cane.

An acetone: water l :l solution of the active ingredient is applied to10 field grown sugar cane plants at a rate equivalent to 4 pounds peracre. At 4 weeks lst Harvest) and 5 weeks (2nd Harvest) afterapplication ofthc compound designated in the table below. 5 of theplants are harvested. aggregated and a random sample removed for sugaranalysis. The analytical methods for sugar content determination havebeen published. See. for instance. Tanimoto. The Press Mel/d ofCum'Analysis. Hawaiian Planters; Record 57(2): 1 33 1964). The data ispresented in Table l below.

Similar results are obtained when phosphonic acid. (2.2.2-trichlorol-hydroxyethyl )-his-[ 2-( 2- hydroxyethoxy) ethyl] ester; phosphonicacid. trichlorol -hydroxycthyl Z-t Z-hydroxypropoxy l methylethyl ester.diester with l.l'-oxydi-Z-propanol; or phosphonic acid.t2.2.2-trichloro-l-hydroxycthyl)-. 2-(Z-hydroxyethoxy) ethyl ester.diester with diethylene glycol. is applied to field grown sugar cane ata rate equivalcntto 4 pounds per acre Sto 8 weeks before harvest.

I claim:

I. A method for increasing sugar yield in field grown.

ripening sugar cane comprising the step of: applying to said sugar caneabout 2 to ll) weeks prior to harvest at a rate equivalent to form about1 pound per acre to.

about lt) pounds per acre of the compound:

a. phosphonic acid. (2.2.2trichlorol hydroxyethyl )-bis-[ 2-(2-hydroxypropoxy )-l methylethyl] ester;

phosphonic acid. (2.2.2-trichlorol hydroxyethyl bis-l 2-(Z-hydroxyethoxy )cthyl] es ter;

0 d 1st Harvest: 2nd Harvest w pol% Juice po1% Juice cane nuritv canenuritv (HO-ZCH -o-cH CH-O) E-IHCCl 10.0 781 Untreated Control 6.2 65.5

i (HO-ZHCH -O-CH -H-O) a imal 12.33 81 .29 11 .65 7 .6

Untreated Control 9.16 753 9.65 78 .61

In the above table pol71 cane is a polarimetric determination and equalsthe percentage of sucrose. it it is the only substance in the solutionwhich will rotate the plane of polarized light. The determination ofp017! cane" is a standard method for determining sucrose content ofsugar cane and is accepted by the industry.

From the data provided above. it can be seen that the test compound.representative of its class as described above, is highly effective forincreasing sucrose yield in cnnur nunn 4. The method according to claim1 wherein the compound is phosphonic acid.(2.2,2-trichloro-lhydroxyethyl 2-( Z-hydroxypropoxy l -methylethylester. diester with l.l -oxydi-2-propanol.

5. The method according to claim I wherein the compound is phosphonicacid. (2,2.2-trichloro-lhydroxyethyl)-. 2-(2-hydroxyethoxy)ethyl ethylester. diester with diethylene glycol.

1. A METHOD FOR INCREASING SUGAR YIELD IN FIELD GROWN, RIPENING SUGARCANE COMPRISING THE STEP OF: APPLYING TO SAID SUGAR CANE ABOUT 2 TO 10WEEKS PRIOR TO HARVEST AT A RATE EQUIVALENT TO FORM ABOUT 1 POUND PERACRE TO ABOUT 10 POUNDS PER ACRE OF THE COMPOUND: A. PHOSPHONIC ACID,(2,2,2-TRICHLORO-1-HYDROXYETHYL)-BIS(2-(2-HYDROXYPROPOXY)-1-METHYLETHYL) ESTER; B. PHOSPHONIC ACID,(2,2,2-TRICHLORO-1-HYDROXYETHYL)-BIS(2-(2-HYDROXYETHOXY)ETHYL) ESTER; C.PHOSPHONIC ACID,(2,2,2-TRUCGKIRI-1-HYDROXYETYL)-,2-(2HYDROXYPROPOXY)-1-METHYLETHYLESTER, DIESTER WITH 1,1OXYDI-2-PROPANOL; OR D. PHOSHONIC ACID,(2,2,2-TRICHLORO-1-HYDROXYETHYL)-, 2-(2HYDROXYETHOXY)ETHYL ESTER,DIESTER WITH DIETHYLENE GLYCOL.
 2. The method according to claim 1wherein the compound is phosphonic acid,(2,2,2-trichloro-1-hydroxyethyl)-bis-(2-(2-hydroxypropoxy)-1-methylethyl)ester.
 3. The method according to claim 1 wherein the compound isphosphonic acid,(2,2,2-trichloro-1-hydroxyethyl)-bis-(2-(2-hydroxyethoxy) ethyl) ester.4. The method according to claim 1 wherein the compound is phosphonicacid, (2,2,2-trichloro-1-hydroxyethyl)-,2-(2-hydroxypropoxy)-1-methylethyl ester, diester with1,1''-oxydi-2-propanol.
 5. The method according to claim 1 wherein thecompound is phosphonic acid, (2,2,2-trichloro-1-hydroxyethyl)-,2-(2-hydroxyethoxy)ethyl ethyl ester, diester with diethylene glycol.